Carbon Dioxide → HCID 68586125, compound

HRID 18452Notes

Reaction equation

HRID 18452 reaction equation
Br[CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:3](OC)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:19](=[O:21])=[O:20].[NH4+].[Cl-].Cl.[CH2:25]([O:27]CC)C>>[CH3:25][O:27][C:15]1[CH:14]=[C:13]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:18]=[CH:17][C:16]=1[C:19]([OH:21])=[O:20]

Participants

6

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 68585664HCID 68585664, compound

Product 1

HCID 68586125HCID 68586125, compoundYield 20%

Procedure

To dry diethyl ether (10 mL) containing Mg turnings (0.24 g; 10 mmol) under N2 was added 1-bromo-2-methoxy-nonyl benzene (3.1 g; 10 mmol). 1,2-Dioiodoethane was added to initiate the reaction. Solid dry Ice (excess) was added after stirring for 1 hour and after additional stirring for 1 hour was added sat. NH4Cl (aq.; 20 mL) and then 4 M HCl (aq.; 2 mL). The organic phase was isolated, dried (MgSO4), filtered and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:5) to yield 600 mg (20%) pure product.

Workup

  1. addition1,2-Dioiodoethane was added
  2. customthe reaction
  3. stirringafter additional stirring for 1 hour
  4. customThe organic phase was isolated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. custompurified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:5)

Sources & evidence

ORD record
ord-09eab05122624a8ab46e6625d81460a4
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

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